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Ketones

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In organic chemistry, a ketone is an organic compound with the structure RC(=O)R', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group (C=O) bonded to two other carbon atoms. If both hydrogen atoms of a formaldehyde are replaced by either alkyl or aryl groups, or one by each, a ketone is obtained.

Aryl groups: Groups derived from arenes by removal of a hydrogen atom from a ring carbon atom. Groups similarly derived from heteroarenes are sometimes subsumed in this definition. E.g. o-tolyl:

Example:
A simple aryl group is phenyl, C6H5; it is derived from benzene. The tolyl group, CH3C6H4, is derived from toluene (methylbenzene). The xylyl group, (CH3)2C6H3, is derived from xylene. Many ketones are known and many have great importance in industry and biology.Examples include many sugars and the industrial solvent acetone.

Ketone group Classes of ketones:

Acetone

Ketones are classified on the basis of their substituents. One broad classification subdivides ketones into symmetrical and unsymmetrical derivatives, depending on the equivalency of the two organic substituents attached to the carbonyl center. Acetone and benzophenone (C6H5C(O)C6H5) are symmetrical ketones. Acetophenone (C6H5C(O)CH3) is an unsymmetrical ketone. In the area of stereochemistry, unsymmetrical ketones are known for being prochiral (compound that can be transferred from achiral to chiral in single step).
Diketone:

respectively. derived from acetone. a symmetrical cyclic ketone. unsymmetrical ketone that is the precursor to other polymers. uncluttered mechanisms for the nucleophilic addition reactions between carbonyl compounds (specifically aldehydes and ketones) and hydrogen cyanide. Dimedone is an example of a cyclic diketone. The most widely used member of this class of compounds is methyl vinyl ketone. Muscone. Larger derivatives exist.3-.3-butanedione. Cyclohexanone. 1. is an animal pheromone. where n varies from 3 for cyclopropanone to the teens. The most important reactions follow from the susceptibility of the carbonyl carbon toward nucleophilic addition and the tendency for the enolates to add to electrophiles. and 1. Chemical Reactions: Ketones engage in many organic reactions. HCN. which is useful in Robinson annulation (a chemical reaction used in organic chemistry for ring formation) reaction. The relative acidity of the α-hydrogen is important in the enolization reactions of ketones and other carbonyl compounds. also known as 2. If you want the mechanisms explained to you in detail. This difference reflects resonance stabilization of the enolate ion that is formed through dissociation. Nucleophilic additions include in approximate order of their generality: THE NUCLEOPHILIC ADDITION OF HYDROGEN CYANIDE TO KETONES: This page gives you the facts and simple. with either stoichiometric and catalytic base. The simplest class have the formula (CH2)nCO.5-dione are examples of 1. is an unsaturated. is an important intermediate in the production of nylon. . CH3C(O)CH=CH2. and hexane-2. 3-methylpentadecanone. The simpliest diketone is diacetyl. Cyclic Ketones: Many ketones are cyclic.A diketone is a molecule containing two ketone groups.2-. Acidity of ketones Ketones are far more acidic (pKa ≈ 20) than a regular alkane (pKa ≈ 50). The acidity of the α-hydrogen also allows ketones and other carbonyl compounds to undergo nucleophilic reactions at that position. Isophorone.4-diketones. Diacetyl. there is a link at the bottom of the page. Unsaturated ketones: Ketones containing alkene and alkyne units are often called unsaturated ketones. acetylacetone.

and the slightly positive carbon atom is attacked by the cyanide ion acting as a nucleophile. Example: With propanone (a ketone) you get 2-hydroxy-2-methylpropanenitrile: The reaction isn't normally done using hydrogen cyanide itself. The carbon-oxygen double bond is highly polar. The mechanism for the addition of HCN to propanone In the first stage. and so will be considered together . The solution will contain hydrogen cyanide (from the reaction between the sodium or potassium cyanide and the sulphuric acid). The mechanisms These are examples of nucleophilic addition. the aldehyde or ketone is mixed with a solution of sodium or potassium cyanide in water to which a little sulphuric acid has been added. The pH of the solution is adjusted to about 4 . because this is an extremely poisonous gas.5. but still contains some free cyanide ions. The reaction of aldehydes and ketones with hydrogen cyanide The facts Hydrogen cyanide adds across the carbon-oxygen double bond in ketones to produce compounds known as hydroxynitriles. This is important for the mechanism. The negative ion formed then picks up a hydrogen ion from somewhere . Instead. because this gives the fastest reaction. from a hydrogen cyanide molecule.Aldehydes and ketones behave identically in their reaction with hydrogen cyanide. there is a nucleophilic attack by the cyanide ion on the slightly positive carbon atom.for example. .although equations and mechanisms will be given for both types of compounds for the sake of completeness.

which would change the CH3CH2 group into some other alkyl group. You could ring the changes on the product by • • changing the nature of the Grignard reagent . changing the nature of the ketone .The hydrogen ion could also come from the water or the H3O+ ions present in the slightly acidic solution.which would change the CH3 groups into whatever other alkyl groups you choose to have in the original ketone. The simplest one is propanone. . The reaction between Grignard reagents and ketones: Ketones have two alkyl groups attached to the carbon-oxygen double bond. This time when you replace the R groups in the general formula for the alcohol produced you get a tertiary alcohol. You don't need to remember all of these. One equation is perfectly adequate. A tertiary alcohol has three alkyl groups attached to the carbon with the -OH attached. The alkyl groups can be any combination of same or different.